How Do You Lead a Global Team Without Time Zone Chaos?

Video Summary

In this episode of Software Leaders Uncensored, host Steve Taplin sits down with Anthony Presley, CTO and co-founder of TimeForge, for an unfiltered conversation on the realities of leading technology in the restaurant industry. From navigating outdated hardware to launching a .NET MAUI rebuild, Presley shares how his global engineering team tackles modernization and compliance at scale. They also dive into the practical applications of AI in development, the importance of strong networks, and lessons from building and selling startups. If you’re a tech leader or entrepreneur in retail, you’ll want to hear this candid discussion.

Key Takeaways

  • Custom Development Powers Growth – Anthony started his career in software early and leveraged custom dev to build scalable solutions in retail and restaurant industries.

  • Legacy Hardware Is a Major Barrier – In restaurant tech, outdated hardware often limits innovation more than software does.

  • Modernizing with .NET MAUI – His team is rebuilding their POS system using .NET MAUI to support multi-platform deployment.

  • AI Tools Are Enhancing Engineering Efficiency – Tools like Lovable and Cursor are helping prototype and streamline development workflows.

  • Team Structure Matters – Presley runs a hybrid global team, leveraging talent in El Salvador, Canada, and the Philippines with a focus on asynchronous communication.

  • Networking Beats Job Boards – Most high-level roles like CTO are filled via relationships, not job applications.

  • Focus on Customers, Not Hype – Presley advises tech leaders to focus on user needs over getting swept up in AI and tech trend headlines.

Participants

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Additional Resources

  • NET MAUI: A Microsoft framework for building cross-platform applications with a single codebase.

  • POS (Point of Sale): Hardware and software used to manage sales transactions in retail and restaurant environments.

  • Cursor: An AI-powered development assistant used for coding and refactoring.

  • Lovable: A tool for prototyping UIs that generates usable front-end code.

  • CTO (Chief Technology Officer): The executive responsible for overseeing a company’s technology strategy and development.

  • PCI Compliance: Standards ensuring secure handling of credit card information.

  • AI Prototyping: Using artificial intelligence to quickly create software mockups or working code samples.

00:00 – Steve Taplin:
Welcome to Software Leaders Uncensored, where tech leaders drop the filters and tell it like it is. I’m your host, Steve Taplin—serial entrepreneur with 30 companies under my belt. 20 failed, 10 succeeded. That rollercoaster inspired my latest book, Fail Hard Win Big, about using failure as fuel.

00:25 – Steve Taplin:
These days, I’m CEO of Scenography Technology. We help businesses build custom enterprise software with top-tier engineers from Latin America. Today, I’m joined by Anthony Presley out of Fort Worth, Texas—founder, advisor, former Chief Product Officer, and currently CTO. Anthony, welcome.

00:50 – Anthony Presley:
Thanks, Steve. Happy to be here. And from our pre-show chat, I already know this will be fun. For the record, I definitely am a tech nerd—no doubt about it.

01:10 – Steve Taplin:
Alright, let’s dive in. Tell us about your career journey.

01:15 – Anthony Presley:
Sure. My story starts overseas. My dad was in the military and stationed abroad. In seventh grade, I learned computers from an Apple Fellow on sabbatical. He introduced me to HyperCard—my first programming language. When we moved back to the States, I didn’t want to flip burgers, so I launched a software company in high school.

01:45 – Anthony Presley:
I built a product called School Lock that let school admins lock down Windows computers. This was 1996—before modern security systems. I got into some trouble with my parents for posting our home number online, but I kept building. Took the company to college and worked for a custom software shop.

02:15 – Anthony Presley:
I did a summer at Raytheon working on stealth ships, then grew a dev shop to 60 people in college. That business collapsed after a client got into trouble with the FTC. We lost 99% of our revenue.

02:40 – Anthony Presley:
I shifted focus to building products, not just custom work. That’s how TimeForge was born—a labor management tool for restaurants. We grew, exited, and I joined another fast-growing software company in Lubbock, Texas. If you’ve shopped in a grocery store in North America, chances are you’ve used our software.

03:30 – Anthony Presley:
In 2020, I joined Custom Business Solutions. We serve about 11,000 restaurants in North America, from Cheesecake Factory to regional brands. It’s been an amazing ride.

04:00 – Steve Taplin:
CTO is a tough role. You have to make tech understandable for non-technical people, work with boards, investors, and explain your value to the CFO. So how did you land the CTO role?

04:35 – Anthony Presley:
It was all about relationships. I had worked with CBS before. When their CTO left, they knew me. They’d seen my work. They had an opening, and that’s all it took.

05:00 – Steve Taplin:
That’s huge. People think jobs come from applying online, but most of the time, it’s your network.

05:15 – Anthony Presley:
Exactly. I know so many engineers who build cool stuff, then get stuck when they spin out because they don’t have the sales chops. Network matters more than people realize.

05:45 – Steve Taplin:
Let’s talk current projects. What are you and your team working on?

06:00 – Anthony Presley:
We’re rebuilding our POS platform using .NET MAUI. The goal is a single codebase that supports Windows, iOS, and Android. We started with Macromedia Flash, then iOS, then Windows—now it’s time for a unified approach.

06:45 – Anthony Presley:
We kicked off the new project this week. One of the biggest constraints in our space is hardware. Restaurant POS systems often run on 10-year-old terminals that need PCI certification. It’s not about modern browsers—it’s about compatibility with old hardware.

07:20 – Steve Taplin:
That’s a brutal limitation. Hardware trumps software in restaurant tech.

07:30 – Anthony Presley:
Exactly. And every credit card provider has their own PCI compliance standards. We have to build for all of them. It’s hard.

08:00 – Steve Taplin:
Tell us about your team structure. How do you manage development?

08:10 – Anthony Presley:
We’ve got about 30 people total. Developers are in Canada, El Salvador, the Philippines. We use contractors as needed. I have three key reports: our product manager, our development manager (based in El Salvador), and our lead architect. The architects break things, then show the team how to rebuild it right.

09:10 – Steve Taplin:
Are you all remote or hybrid?

09:15 – Anthony Presley:
Hybrid. Some roles need to be onsite because of hardware. We do staging and testing in our office—things like setting up 30 terminals and simulating transactions with real credit card devices. You can’t do that remotely.

10:00 – Steve Taplin:
So, what are your biggest challenges as CTO right now?

10:05 – Anthony Presley:
Two things: the .NET MAUI rebuild and figuring out how to integrate AI smartly. There’s a lot of hype. Everyone wants AI, but you have to handle it responsibly, especially with customer data. And you have to be practical.

10:40 – Anthony Presley:
I’ve been building AI systems since 2007. I remember showing a labor scheduler to a CEO, and he said, “I already pay my managers to do that.” Now, of course, everyone wants automation.

11:10 – Anthony Presley:
We use tools like Cursor for AI-assisted coding and Lovable for mockups. They’re great for prototyping and accelerating development. But you still have to validate everything.

12:10 – Steve Taplin:
Have you deployed anything from Lovable in production yet?

12:15 – Anthony Presley:
Not yet, but the code is promising. It’s real code, not just mockups. Cursor, on the other hand, we’ve used in several places. Pricing changes annoyed some folks, but it’s still valuable.

13:00 – Steve Taplin:
So how do you even keep up with all these AI tools?

13:05 – Anthony Presley:
It’s exhausting. There was a point last year where every two weeks a new tool would become the “best one.” Eventually, we just had to pause and be selective.

13:40 – Steve Taplin:
What’s next for your AI stack?

13:45 – Anthony Presley:
We’re exploring tools for automated code review. Haven’t settled yet. CoPilot, WindSurf—they all have strengths. But by the time this airs, the landscape could change again.

14:20 – Steve Taplin:
Alright, let’s shift. What’s a hard lesson you’d go back and teach your younger self?

14:30 – Anthony Presley:
Build your network. Engineers often focus so much on product that they forget to invest in relationships. But those connections open doors—whether you’re job hunting or launching a company.

15:10 – Steve Taplin:
Yep, and the best engineers are usually the ones with their headphones on, not networking.

15:20 – Anthony Presley:
Totally. But if you want to lead or move up, you need to start planting those relationship seeds early.

15:45 – Steve Taplin:
Your team is global. How do you manage time zone challenges?

15:50 – Anthony Presley:
We mostly work async. Tools like DailyBot help with standups. We use Kanban and sometimes run sprints. Weekly or biweekly calls are at flexible times so everyone can attend.

16:30 – Anthony Presley:
We try to keep most folks within a few hours of Central Time. Montreal, El Salvador, and Latin America work great. The Philippines is a stretch, but our team there is flexible.

17:00 – Steve Taplin:
Awesome. You’ve clearly built something solid. Before we wrap, any final advice for tech leaders out there?

17:10 – Anthony Presley:
Focus. There’s always going to be noise—AI hype, headlines about the latest disruption. Don’t chase every trend. Talk to your users, listen, and build good products. That’s what matters.

17:35 – Steve Taplin:
Perfect way to close. Anthony, thank you so much for getting uncensored with us today. To our listeners—thanks for tuning in. If you liked the show, hit subscribe. If you didn’t, tell your competitors. They could probably use the help.

18:00 – Steve Taplin:
And don’t forget to check out Fail Hard Win Big. If you need help building great software, my team at Scenography Technology is ready to go. Thanks again, everyone!

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